[Bis(pyridin-2-ylmeth­yl) ether]trichlorido­rhodium(III) dichloro­methane monosolvate: unusual hydrolysis of the methyl­ene bridge in (pyrazolylmeth­yl)pyridine

Ojwach, S.O.; Omondi, B.; Darkwa, J.

doi:10.1107/S1600536811027644

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1097

doi:10.1107/S1600536811027644

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[Bis(pyridin-2-ylmethyl) ether]trichloridorhodium(III) dichloromethane monosolvate: unusual hydrolysis of the methylene bridge in (pyrazolylmethyl)pyridine

Stephen O. Ojwach,^a Bernard Omondi ^b ^* and James Darkwa ^a

^aDepartment of Chemistry, University of Johannesburg, Auckland Park Kingsway Campus, PO Box 524, Johannesburg, South Africa, and ^bSchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
^*Correspondence e-mail: owaga@ukzn.ac.za

(Received 14 June 2011; accepted 11 July 2011; online 16 July 2011)

In the title compound, [RhCl₃(C₁₂H₁₂N₂O)]·CH₂Cl₂, the Rh^III atom shows a slightly distorted octahedral geometry being coordinated by two N atoms and one O atom from the 2,2′-(oxydimethanediyl)dipyridine ligand and three Cl atoms. Two Cl atoms adopt a trans arrangement to the two pyridyl N atoms, while the third Cl atom and the O atoms occupy the axial site. The Rh—Cl bonds that are trans to the pyridyl N atoms are slightly longer than the Rh—Cl bond distance trans to the O atom.

Related literature

For hydrogenation of olefins, see: Samec et al. (2006 ); Xu et al. (2009 ); Chalid et al. (2011 ); Liu et al. (2011 ). For multidentate N-containing ligands, see: Dayan & Centikaya (2007 ); Deng et al. (2005 ). For pyrazolyl-based transition metal complexes as catalysts, see: Ojwach & Darkwa (2010 ) and references therein. For structures bearing the 2,2′-(oxydimethanediyl)dipyridine ligand, see: Nanty et al. (2000 ) and references therein.

Experimental

Crystal data

[RhCl₃(C₁₂H₁₂N₂O)]·CH₂Cl₂
M_r = 494.42
Monoclinic, P 2₁ /c
a = 9.5360 (18) Å
b = 12.527 (2) Å
c = 14.340 (3) Å
β = 95.071 (4)°
V = 1706.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.78 mm⁻¹
T = 100 K
0.14 × 0.13 × 0.05 mm

Data collection

Bruker X8 APEXII 4K KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.788, T_max = 0.916
30694 measured reflections
4276 independent reflections
2925 reflections with I > 2σ(I)
R_int = 0.102

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.139
S = 1.08
4276 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 1.50 e Å⁻³
Δρ_min = −1.25 e Å⁻³

Table 1
Selected bond lengths (Å)

N1—Rh1	2.037 (5)
N2—Rh1	2.031 (5)
O1—Rh1	2.069 (4)
Cl1—Rh1	2.3479 (15)
Cl2—Rh1	2.2941 (15)
Cl3—Rh1	2.3315 (15)

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus and XPREP (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811027644/om2440sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027644/om2440Isup2.hkl

checkCIF report

Comment top

Transition metal catalyzed hydrogenation of olefins constitutes one of the most important reactions in fine chemicals and petroleum industries (Samec et al., 2006, Xu et al., 2009). To date most hydrogenation catalysts reported in literature are based on phosphine ruthenium and rhodium complexes (Chalid et al., 2011, Liu et al., 2011). Recently multidentate nitrogen-containing ligands such as 2,6-bis(imino)pyridine (Dayan & Centikaya, 2007, and 2,6(3,5-dimethylpyrazol-1-yl)pyridine (Deng et al., 2005), have attracted much attention, and have been used as effective catalysts for transfer hydrogenation of ketones. As part of our investigation of pyrazolyl-based transition metal complexes as catalysts for various olefin transformations (Ojwach and Darkwa, 2010 and references therein), we are currently exploring the ability of (pyrazolylmethyl)pyridine ruthenium and rhodium complexes to catalyze olefin hydrogenation reactions. On one such attempt to synthesize the rhodium complex of 2-(3,5-dimethylpyrazol-1-ylmethyl)pyridine, the title compound was obtained. This transformation points to the possible hydrolysis of the 2-(3,5-dimethylpyrazol-1-ylmethyl)pyridine compound promoted by RhCl₃.6H₂O salt to form the (pyridinylmethyl)ether ligand in the title compound.

In the title compound [RhCl₃(C₁₂H₁₂N₂O)].CH₂Cl₂ the asymmetric unit contains one molecule of the Rh^III complex and a dichloromethane molecule of solvation (Fig. 1). In the structure, the Rh atom center is in an octahedral environment with two nitrogen atoms from 2,2'-(oxydimethanediyl)dipyridine ligand trans to two chlorine atoms in the equatorial position. The axial positions are occupied by a third chlorine atom and the oxygen atom from 2,2'-(oxydimethanediyl)dipyridine. 2,2'-(oxydimethanediyl)dipyridine acts as an N,O,N' tridentate ligand in which the angles around the the Rh metal center are close to orthogonal (see Table 1). The bond distances for the Cl atoms to the Rh atom are longer for the Cl atoms trans to the pyridyl N atoms of the 2,2'-(oxydimethanediyl)dipyridine ligand (2.3315 (15) and 2.3479 (15) Å) as compared to the distance of the Cl atom trans to the O atom (2.2941 (5) Å). A similar trend is observed in closely related compounds with the same ligand system where metal–ligand bond distance that is trans to the ether ligand was found to be statistically shorter than the distance between the trans ligands to pyridyl N atoms (the trans effect) (Nanty et al., 2000 and references therein). The Rh atom is slightly off the equatorial plane N₂Cl₂ and is inclined toward the axial Cl atom as the bond angles N–Rh–Cl would suggest (172.82 (13) and 172.89 (14)°). The O–Rh–Cl bond angle is 176.29 (12)° also pointing to a slight inclination of the Rh toward the equatorial Cl atoms.

Related literature top

For hydrogenation of olefins, see: Samec et al. (2006); Xu et al. (2009); Chalid et al. (2011); Liu et al. (2011). For multidentate N-containing ligands, see: Dayan & Centikaya (2007); Deng et al. (2005). For pyrazolyl-based transition metal complexes as catalysts, see: Ojwach & Darkwa (2010) and references therein. For structures bearing the 2,2'-(oxydimethanediyl)dipyridine ligand, see: Nanty et al. (2000) and refereneces therein.

Experimental top

To a solution of RhCl₃.6H₂O (0.20 g, 0.60 mmol) in MeOH (10 ml) was added a solution of 2-(3,5-dimethylpyazol-1-ylmethyl)pyridine (0.12 g, 0.60 mmol) in MeOH (10 ml) and the resultant orange solution was stirred for 24 h. After the reaction period, the solution was filtered off and solvent removed in vacuo to afford an orange solid. Recrystallization of the crude product from chloroform gave single crystals suitable for X-ray analysis. The crystals were insoluble in most organic solvents. Yield = 0.09 g (40%).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus and XPREP (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

[Bis(pyridin-2-ylmethyl) ether]trichloridorhodium(III) dichloromethane monosolvate top

Crystal data top

[RhCl₃(C₁₂H₁₂N₂O)]·CH₂Cl₂	F(000) = 976
M_r = 494.42	D_x = 1.925 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 31705 reflections
a = 9.5360 (18) Å	θ = 2.1–28.6°
b = 12.527 (2) Å	µ = 1.78 mm⁻¹
c = 14.340 (3) Å	T = 100 K
β = 95.071 (4)°	Block, brown
V = 1706.3 (6) Å³	0.14 × 0.13 × 0.05 mm
Z = 4

Data collection top

Bruker X8 APEXII 4K KappaCCD diffractometer	2925 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.102
ϕ and ω scans	θ_max = 28.6°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
T_min = 0.788, T_max = 0.916	k = −15→16
30694 measured reflections	l = −19→19
4276 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0602P)² + 6.0697P] where P = (F_o² + 2F_c²)/3
4276 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 1.50 e Å⁻³
0 restraints	Δρ_min = −1.25 e Å⁻³

Crystal data top

[RhCl₃(C₁₂H₁₂N₂O)]·CH₂Cl₂	V = 1706.3 (6) Å³
M_r = 494.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5360 (18) Å	µ = 1.78 mm⁻¹
b = 12.527 (2) Å	T = 100 K
c = 14.340 (3) Å	0.14 × 0.13 × 0.05 mm
β = 95.071 (4)°

Data collection top

Bruker X8 APEXII 4K KappaCCD diffractometer	4276 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2925 reflections with I > 2σ(I)
T_min = 0.788, T_max = 0.916	R_int = 0.102
30694 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.08	Δρ_max = 1.50 e Å⁻³
4276 reflections	Δρ_min = −1.25 e Å⁻³
199 parameters

Special details top

Experimental. The intensity data was collected on a Bruker X8 Apex 4 K CCD diffractometer using an exposure time of 20 sec/per frame. A total of 3527 frames were collected with a frame width of 0.5° covering upto θ = 28.57° with 99.8% completeness accomplished.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. >>> The Following ALERTS were generated <<< Format: alert-number_ALERT_alert-type_alert-level text 973_ALERT_2_B Large Calcd. Positive Residual Density on Rh1 1.53 e A-3 Difference map does not reveal any missing peaks, R factor is 4.8% 342_ALERT_3_C Low Bond Precision on C—C Bonds (x 1000) Ang.. 9 083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large. 6.07 960_ALERT_3_G Number of Intensities with I. LT. - 2*sig(I).. 7 912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 76

Noted.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.9453 (6)	0.3170 (5)	0.5707 (4)	0.0220 (12)
C2	0.9516 (6)	0.3990 (5)	0.6344 (4)	0.0250 (13)
H2	0.9982	0.3893	0.6952	0.03*
C3	0.8896 (7)	0.4959 (5)	0.6095 (4)	0.0286 (14)
H3	0.8936	0.5538	0.6525	0.034*
C4	0.8218 (7)	0.5068 (5)	0.5210 (4)	0.0284 (14)
H4	0.7789	0.5727	0.5022	0.034*
C5	0.8166 (6)	0.4224 (5)	0.4604 (4)	0.0238 (13)
H5	0.7684	0.43	0.3999	0.029*
C6	1.0152 (6)	0.2118 (5)	0.5914 (4)	0.0213 (12)
H6A	1.1158	0.2167	0.5797	0.026*
H6B	1.0101	0.194	0.6583	0.026*
C7	0.8409 (6)	0.0651 (5)	0.5762 (4)	0.0240 (13)
H7A	0.8595	0.0672	0.6452	0.029*
H7B	0.8459	−0.0103	0.556	0.029*
C8	0.6967 (6)	0.1079 (5)	0.5489 (4)	0.0217 (12)
C9	0.5837 (6)	0.0877 (5)	0.6005 (4)	0.0248 (13)
H9	0.5973	0.05	0.6581	0.03*
C10	0.4508 (7)	0.1230 (5)	0.5677 (4)	0.0285 (14)
H10	0.372	0.11	0.6023	0.034*
C11	0.4352 (6)	0.1776 (5)	0.4833 (4)	0.0284 (14)
H11	0.3447	0.2014	0.4589	0.034*
C12	0.5499 (6)	0.1970 (5)	0.4353 (4)	0.0272 (13)
H12	0.5381	0.2353	0.378	0.033*
C13	0.5353 (9)	0.4120 (7)	0.6578 (7)	0.053 (2)
H13A	0.6165	0.3889	0.7009	0.064*
H13B	0.5467	0.3812	0.5953	0.064*
N1	0.8778 (5)	0.3292 (4)	0.4846 (3)	0.0179 (10)
N2	0.6797 (5)	0.1632 (4)	0.4675 (3)	0.0212 (10)
O1	0.9483 (4)	0.1273 (3)	0.5336 (3)	0.0204 (8)
Cl1	1.08727 (15)	0.21896 (12)	0.35869 (10)	0.0231 (3)
Cl2	0.76119 (16)	0.27205 (13)	0.27541 (10)	0.0255 (3)
Cl3	0.83695 (15)	0.02382 (12)	0.33886 (9)	0.0231 (3)
Cl4	0.5347 (2)	0.55102 (18)	0.64998 (18)	0.0583 (6)
Cl5	0.3773 (2)	0.36285 (18)	0.69904 (14)	0.0513 (5)
Rh1	0.86208 (5)	0.19166 (4)	0.40861 (3)	0.01818 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.020 (3)	0.023 (3)	0.025 (3)	−0.002 (2)	0.010 (2)	0.002 (2)
C2	0.026 (3)	0.028 (4)	0.021 (3)	−0.007 (3)	0.006 (2)	0.003 (2)
C3	0.037 (4)	0.018 (3)	0.032 (3)	−0.002 (3)	0.014 (3)	−0.004 (2)
C4	0.030 (3)	0.018 (3)	0.039 (3)	0.003 (2)	0.011 (3)	0.002 (3)
C5	0.023 (3)	0.025 (3)	0.024 (3)	0.002 (2)	0.006 (2)	0.006 (2)
C6	0.018 (3)	0.019 (3)	0.026 (3)	−0.001 (2)	0.001 (2)	−0.001 (2)
C7	0.025 (3)	0.023 (3)	0.024 (3)	−0.002 (2)	0.007 (2)	0.005 (2)
C8	0.023 (3)	0.018 (3)	0.024 (3)	−0.003 (2)	0.005 (2)	0.000 (2)
C9	0.026 (3)	0.025 (3)	0.024 (3)	−0.007 (3)	0.007 (2)	−0.002 (2)
C10	0.023 (3)	0.029 (4)	0.035 (3)	−0.006 (3)	0.010 (3)	−0.006 (3)
C11	0.016 (3)	0.029 (4)	0.039 (3)	−0.002 (2)	−0.001 (2)	−0.004 (3)
C12	0.024 (3)	0.027 (4)	0.029 (3)	−0.004 (3)	0.000 (2)	−0.005 (3)
C13	0.042 (5)	0.040 (5)	0.077 (6)	0.013 (4)	0.008 (4)	0.013 (4)
N1	0.016 (2)	0.016 (3)	0.023 (2)	−0.0009 (18)	0.0045 (18)	0.0013 (18)
N2	0.020 (2)	0.021 (3)	0.023 (2)	−0.0013 (19)	0.0039 (19)	−0.0011 (19)
O1	0.018 (2)	0.022 (2)	0.0219 (19)	−0.0005 (16)	0.0038 (15)	0.0005 (16)
Cl1	0.0195 (7)	0.0223 (8)	0.0283 (7)	−0.0014 (5)	0.0060 (5)	−0.0002 (5)
Cl2	0.0257 (7)	0.0280 (8)	0.0227 (7)	0.0011 (6)	0.0018 (5)	0.0037 (6)
Cl3	0.0247 (7)	0.0205 (8)	0.0244 (6)	−0.0026 (6)	0.0041 (5)	−0.0008 (5)
Cl4	0.0419 (12)	0.0495 (13)	0.0855 (16)	0.0110 (9)	0.0173 (11)	0.0111 (11)
Cl5	0.0472 (12)	0.0535 (13)	0.0525 (11)	0.0010 (9)	0.0010 (9)	0.0028 (9)
Rh1	0.0174 (2)	0.0170 (2)	0.0204 (2)	−0.00075 (18)	0.00326 (15)	0.00144 (18)

Geometric parameters (Å, º) top

C1—N1	1.349 (7)	C8—C9	1.383 (8)
C1—C2	1.373 (8)	C9—C10	1.385 (9)
C1—C6	1.495 (8)	C9—H9	0.95
C2—C3	1.384 (9)	C10—C11	1.387 (9)
C2—H2	0.95	C10—H10	0.95
C3—C4	1.380 (9)	C11—C12	1.365 (8)
C3—H3	0.95	C11—H11	0.95
C4—C5	1.367 (9)	C12—N2	1.350 (8)
C4—H4	0.95	C12—H12	0.95
C5—N1	1.336 (7)	C13—Cl4	1.745 (9)
C5—H5	0.95	C13—Cl5	1.777 (9)
C6—O1	1.456 (7)	C13—H13A	0.99
C6—H6A	0.99	C13—H13B	0.99
C6—H6B	0.99	N1—Rh1	2.037 (5)
C7—O1	1.462 (7)	N2—Rh1	2.031 (5)
C7—C8	1.496 (8)	O1—Rh1	2.069 (4)
C7—H7A	0.99	Cl1—Rh1	2.3479 (15)
C7—H7B	0.99	Cl2—Rh1	2.2941 (15)
C8—N2	1.355 (7)	Cl3—Rh1	2.3315 (15)

N1—C1—C2	120.8 (5)	C12—C11—C10	120.0 (6)
N1—C1—C6	116.8 (5)	C12—C11—H11	120
C2—C1—C6	122.3 (5)	C10—C11—H11	120
C1—C2—C3	119.5 (6)	N2—C12—C11	121.5 (6)
C1—C2—H2	120.2	N2—C12—H12	119.2
C3—C2—H2	120.2	C11—C12—H12	119.2
C4—C3—C2	118.6 (6)	Cl4—C13—Cl5	111.6 (4)
C4—C3—H3	120.7	Cl4—C13—H13A	109.3
C2—C3—H3	120.7	Cl5—C13—H13A	109.3
C5—C4—C3	119.8 (6)	Cl4—C13—H13B	109.3
C5—C4—H4	120.1	Cl5—C13—H13B	109.3
C3—C4—H4	120.1	H13A—C13—H13B	108
N1—C5—C4	121.3 (6)	C5—N1—C1	119.9 (5)
N1—C5—H5	119.3	C5—N1—Rh1	126.1 (4)
C4—C5—H5	119.3	C1—N1—Rh1	113.5 (4)
O1—C6—C1	111.2 (5)	C12—N2—C8	119.4 (5)
O1—C6—H6A	109.4	C12—N2—Rh1	126.6 (4)
C1—C6—H6A	109.4	C8—N2—Rh1	114.0 (4)
O1—C6—H6B	109.4	C6—O1—C7	116.0 (4)
C1—C6—H6B	109.4	C6—O1—Rh1	109.3 (3)
H6A—C6—H6B	108	C7—O1—Rh1	109.3 (3)
O1—C7—C8	111.2 (5)	N2—Rh1—N1	87.23 (19)
O1—C7—H7A	109.4	N2—Rh1—O1	81.99 (17)
C8—C7—H7A	109.4	N1—Rh1—O1	82.03 (17)
O1—C7—H7B	109.4	N2—Rh1—Cl2	96.40 (14)
C8—C7—H7B	109.4	N1—Rh1—Cl2	94.57 (13)
H7A—C7—H7B	108	N2—Rh1—Cl3	87.75 (14)
N2—C8—C9	121.0 (6)	O1—Rh1—Cl3	92.19 (12)
N2—C8—C7	116.5 (5)	Cl2—Rh1—Cl3	91.09 (6)
C9—C8—C7	122.4 (5)	N1—Rh1—Cl1	90.78 (13)
C8—C9—C10	119.5 (6)	O1—Rh1—Cl1	90.98 (11)
C8—C9—H9	120.2	Cl2—Rh1—Cl1	90.56 (5)
C10—C9—H9	120.2	Cl3—Rh1—Cl1	93.59 (5)
C9—C10—C11	118.5 (6)	N1—Rh1—Cl3	172.82 (13)
C9—C10—H10	120.7	N2—Rh1—Cl1	172.89 (14)
C11—C10—H10	120.7	O1—Rh1—Cl2	176.29 (12)

N1—C1—C2—C3	−0.9 (9)	C12—N2—Rh1—N1	87.7 (5)
C6—C1—C2—C3	177.4 (5)	C8—N2—Rh1—N1	−89.7 (4)
C1—C2—C3—C4	0.6 (9)	C12—N2—Rh1—O1	170.1 (5)
C2—C3—C4—C5	0.4 (9)	C8—N2—Rh1—O1	−7.3 (4)
C3—C4—C5—N1	−1.0 (9)	C12—N2—Rh1—Cl2	−6.6 (5)
N1—C1—C6—O1	−25.6 (7)	C8—N2—Rh1—Cl2	176.1 (4)
C2—C1—C6—O1	156.1 (5)	C12—N2—Rh1—Cl3	−97.4 (5)
O1—C7—C8—N2	24.6 (7)	C8—N2—Rh1—Cl3	85.2 (4)
O1—C7—C8—C9	−158.8 (5)	C12—N2—Rh1—Cl1	161.6 (9)
N2—C8—C9—C10	1.2 (9)	C8—N2—Rh1—Cl1	−15.8 (15)
C7—C8—C9—C10	−175.2 (6)	C5—N1—Rh1—N2	−84.2 (5)
C8—C9—C10—C11	0.1 (9)	C1—N1—Rh1—N2	88.5 (4)
C9—C10—C11—C12	−1.1 (9)	C5—N1—Rh1—O1	−166.5 (5)
C10—C11—C12—N2	0.8 (10)	C1—N1—Rh1—O1	6.2 (4)
C4—C5—N1—C1	0.7 (8)	C5—N1—Rh1—Cl2	12.0 (5)
C4—C5—N1—Rh1	173.0 (4)	C1—N1—Rh1—Cl2	−175.3 (3)
C2—C1—N1—C5	0.3 (8)	C5—N1—Rh1—Cl3	−129.9 (10)
C6—C1—N1—C5	−178.1 (5)	C1—N1—Rh1—Cl3	42.8 (13)
C2—C1—N1—Rh1	−172.9 (4)	C5—N1—Rh1—Cl1	102.6 (4)
C6—C1—N1—Rh1	8.7 (6)	C1—N1—Rh1—Cl1	−84.7 (4)
C11—C12—N2—C8	0.6 (9)	C6—O1—Rh1—N2	−107.8 (3)
C11—C12—N2—Rh1	−176.7 (5)	C7—O1—Rh1—N2	20.1 (4)
C9—C8—N2—C12	−1.6 (9)	C6—O1—Rh1—N1	−19.5 (3)
C7—C8—N2—C12	175.1 (5)	C7—O1—Rh1—N1	108.4 (4)
C9—C8—N2—Rh1	176.0 (4)	C6—O1—Rh1—Cl2	−43 (2)
C7—C8—N2—Rh1	−7.4 (7)	C7—O1—Rh1—Cl2	84.6 (19)
C1—C6—O1—C7	−95.4 (5)	C6—O1—Rh1—Cl3	164.8 (3)
C1—C6—O1—Rh1	28.7 (5)	C7—O1—Rh1—Cl3	−67.3 (3)
C8—C7—O1—C6	95.3 (5)	C6—O1—Rh1—Cl1	71.2 (3)
C8—C7—O1—Rh1	−28.7 (5)	C7—O1—Rh1—Cl1	−161.0 (3)

Experimental details

Crystal data
Chemical formula	[RhCl₃(C₁₂H₁₂N₂O)]·CH₂Cl₂
M_r	494.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.5360 (18), 12.527 (2), 14.340 (3)
β (°)	95.071 (4)
V (Å³)	1706.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.78
Crystal size (mm)	0.14 × 0.13 × 0.05

Data collection
Diffractometer	Bruker X8 APEXII 4K KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.788, 0.916
No. of measured, independent and observed [I > 2σ(I)] reflections	30694, 4276, 2925
R_int	0.102
(sin θ/λ)_max (Å⁻¹)	0.673

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.139, 1.08
No. of reflections	4276
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.50, −1.25

Computer programs: APEX2 (Bruker, 2007), SAINT-Plus (Bruker, 2007), SAINT-Plus and XPREP (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005) and ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

N1—Rh1	2.037 (5)	Cl1—Rh1	2.3479 (15)
N2—Rh1	2.031 (5)	Cl2—Rh1	2.2941 (15)
O1—Rh1	2.069 (4)	Cl3—Rh1	2.3315 (15)

N2—Rh1—N1	87.23 (19)	N1—Rh1—Cl1	90.78 (13)
N2—Rh1—O1	81.99 (17)	O1—Rh1—Cl1	90.98 (11)
N1—Rh1—O1	82.03 (17)	Cl2—Rh1—Cl1	90.56 (5)
N2—Rh1—Cl2	96.40 (14)	Cl3—Rh1—Cl1	93.59 (5)
N1—Rh1—Cl2	94.57 (13)	N1—Rh1—Cl3	172.82 (13)
N2—Rh1—Cl3	87.75 (14)	N2—Rh1—Cl1	172.89 (14)
O1—Rh1—Cl3	92.19 (12)	O1—Rh1—Cl2	176.29 (12)
Cl2—Rh1—Cl3	91.09 (6)

Acknowledgements

We thank the NRF and the University of Johannesburg for financial support.

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